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Fall Harvest Wine Trail Sep 27-Oct 02, 2021

  • Catered Dinner in Vineyard
  • Professional Photographer
  • Grape Harvesting
  • 10 local wineries
  • Pottery Wheel
  • Shakespeare Festival
  • Lithia Park Picnic
  • Historic Jacksonville Trolley tour
  • Harry and David Country store
  • Happy Hour events
  • Crater Lake or Fall Redwoods

Fall Harvest Wine Trail

The Rogue River area of Southern Oregon was named one of the New York Times 52 Places to Travel in 2018. The beautiful town of Ashland hosts the ever-popular Shakespeare Festival since 1935 which traces its roots back to the Chautauqua movement bringing culture and entertainment to rural areas in the late 19th century.  Natural beauty, a vibrant arts community and an ideal wine growing Mediterranean climate come together on this not to be missed tour! We’ll visit, sample and learn from over 10 wineries in this region. We’ve crafted Exciting, Private, and Elite experiences just for you!

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Starting at $1679 per person Book Now or call us: 1-877-232-8687
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  • Private Catered Dinner in Vineyard
  • Professional Photographer available for Vineyard shoots
  • Hands on Grape Harvesting
  • Visit over 10 local wineries for tasting and learning
  • Spin and Sip with wine and Pottery Wheel Experience
  • Backstage Oregon Shakespeare Festival
  • Exploring the flora and fauna of Lithia Park followed by Picnic
  • Historic Jacksonville Trolley tour
  • Learn about Hemp and hands on experience
  • Visit Harry and David Country store
  • Local creamery, chocolate, beer and cider tastings
  • Two elite Happy Hour events in secret magical locations
  • Day trip to Crater Lake or Fall Redwoods
  • Fall Color Drive through Southern Oregon
  • Bustling delicious Ashland Food Scene along with live music venues

What's Included

  • 5-night hotel accommodations
  • 4 Breakfasts
  • 2 Lunches
  • 2 Dinners
  • 3 Magic Hours
  • Vineyard Visits
  • Wine Tasting at ___ Vineyards
  • Grape Harvesting
  • Pottery Wheel Throwing
  • Backstage Tour of at the Oregon Shakespeare Festival
  • Historic Trolley Tour in Jacksonville
  • Guided tour of Lithia Park
  • Visit to either Crater Lake OR Giant Redwood Forest
  • Transportation during tours
  • Gratuities for Local Guides

What's Not Included

  • Airfare
  • Airport Transfers
  • Meals not specified
  • Alcohol not specified
  • Gratuities for your Tour Concierge


Location Map for Fall Harvest Wine Trail
  • DAY 1:»

    Our tour begins with a *First Crush Magic Hour. We’ll meet at our hotel, The Ashland Hills, a locally owned and inspired gem, where we’ll whisk you off to our first secret afternoon Winery Experience. After watching the sunset on the Siskiyou range, we will head to the charming Ashland downtown area for dinner on your own at one of many incredible venues.
    Meals Included: Magic Hour

  • DAY 2:»

    We’ll wake up early and head to a nearby winery to watch the sun rise over the hills as we help a local vintner harvest grapes. We will offer a continental breakfast of local juice and pastries while harvesting to take in the beauty around you. After, head back to the hotel for free time relaxing by the pool, get a massage, grab lunch, or head into town for a few hours of exploring, shopping and dining. Early afternoon we will get our hands dirty while learning the basics of pottery wheel throwing. You will design a small pot which will be fired, and hand printed for you by a local artist and be ready by departure. Evening and dinner on your own to explore walking the quaint streets of Ashland.
    Meals Included: Breakfast, Wine Tasting

  • DAY 3:»

    After Breakfast at the Hotel, we’ll get a Backstage Tour at the Oregon Shakespeare Festival. Wednesday will be a free night with option to see a show. If you haven’t yet purchased tickets, this is a great opportunity to see what’s available and get inspired by this amazing annual production where actors come from around the world to perform. Next up, we venture to the nearby town of Jacksonville where we will take a Historic Trolley tour through the town followed by free time for shopping and lunch on your own. After lunch, we visit a few more wineries, have some tastings, and experience unbelievable views. We finish this afternoon with a Private Dinner complete with wine pairings inside a picturesque Vineyard.
    Meals Included: Breakfast, Dinner

  • DAY 4:»

    Breakfast at the Hotel followed by a guided tour through Lithia Park, coined the Crown Jewel of Ashland for over 100 years. John Mclaren, also the designer of San Francisco’s Golden Gate Park, was the landscape architect. After the tour, we will meet for a quintessential picnic in the park. After lunch, there is free time to explore, shop, hike, more wine tasting or sit poolside. Tonight, is the optional Oregon Shakespeare Performance at 8:00 pm so beforehand, we will meet for Magic Hour at one of Ashland’s amazing locations.
    Meals Included: Breakfast, Lunch, Magic Hour

  • DAY 5:»

    Breakfast at Hotel then we are off on an Adventure to visit the famous Crater Lake or the Giant Redwood Forest. We will base our destination on what the weather has in store for us the week of our scheduled tour. Both are equally amazing! More winery visits and tasting on the return trip along with incredible West Coast Fall Color preview. We end our afternoon at a surprise location before heading back to our hotel for our final night in Ashland.
    Meals Included: Breakfast, Lunch, Magic Hour/Dinner

Why We Go Local

Our Experience Going Local

We spend weeks in each location to design our itineraries with amazing hidden gems and experiences rich in culture. By personally scouting our tours, we ensure to deliver experiences you may never have found on your own. We not only make connections along the way, we make friends and hand select our guides for their knowledge, guest interaction, and find the fun mentality. Instead of planning a tour behind a computer desk, we go live it by going local and taking the roads less travelled. We connect with our local guides that help us reach people in places where we can be of service. We’ve woven into many of our trips the opportunity to give back. Travel with us and discover a region through its people, culture and food while treading lightly on Gorgeous Lands.

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Additional Information

Book this tour to Oregon on September 27th.

Starting at $1679 per person

Book Now

or call us: 1-877-232-8687

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